Catalyst Control over X-Fold Stereogenicity

Informations projet

X-Fold StereoGen

N° de convention de subvention: 101002471

DOI

10.3030/101002471

Projet clôturé

Date de signature de la CE 17 Decembre 2020

Date de début 1 Mai 2021

Date de fin 30 Avril 2026

Financé au titre de

• EXCELLENT SCIENCE - European Research Council (ERC)

Coût total

€ 1 999 266,00

Contribution de l’UE

€ 1 999 266,00

Coordonné par

UNIVERSITAT BASEL
Switzerland

Periodic Reporting for period 3 - X-Fold StereoGen (Catalyst Control over X-Fold Stereogenicity)

Période du rapport: 2024-05-01 au 2025-10-31

Résumé du contexte et des objectifs généraux du projet

Stereoisomers are molecules which have the same connectivity, but different arrangements of atoms in space, resulting in distinct properties such as bioactivity. Preparing the desired stereoisomer therefore requires control over the configuration of the groups in the molecule which define stereoisomerism and thus encode molecular topology. Stereoselective catalysis is thereby considered as ideal approach to guide chemical reactions to pathways to give the required stereoisomers. Furthermore, the prospects of minimal side- and byproducts facilitates purifications. While previous catalytic methods were selective for stereogenic units with two configurations, the aim of this EU-funded X-Fold StereoGen project is to catalytically control stereogenic units that encode more than two configurations.

This will allow scientists and ultimately society to catalytically address a larger, nonbinary stereochemical space. The higher-order stereogenic units are controlled with more sustainable synthetic methods to selectively access desired compounds with the required molecular topologies.

The overall objective is to establish the feasibility of catalyst control over higher-order stereogenicity for units with 3-6 configurations. The conceptual relationship between the molecular conformations and higher-order stereogenicity is thereby emphasized. Additionally, the diversity of the increased stereochemical space addressable by catalysis is explored.

Travail effectué depuis le début du projet jusqu’à la fin de la période considérée dans le rapport et principaux résultats atteints jusqu’à présent

The work performed so far allowed to establish the feasibility to catalytically control three-, four- and sixfold stereogenicity. Combinations of two catalysts thereby guided oxidation reactions to form each of the three possible stereoisomers. Furthermore, fourfold stereogenicity was addressed for the synthesis of overcrowded alkenes in a two-step process, while catalyst control over sixfold stereogenicity was rendered feasible by forming an aromatic ring.

Progrès au-delà de l’état des connaissances et impact potentiel prévu (y compris l’impact socio-économique et les conséquences sociétales plus larges du projet jusqu’à présent)

Besides rotationally restricted compounds, high-valent stereocenters with more than two configurations were addressed by stereoselective catalysis. We expect that by the end of the project, a diversity of higher-order stereogenic units with three-to-six configurations will become catalytically tractable.

Catalyst control over pentavalent stereocentres